The Bad Guys Know It Too
by TiTivillus
Summary: Somebody from John's past is looking to settle an old score by going after Sam and Dean. Pre-Series. TeenChesters. ProtectiveBigBro!Dean. Hurt!Boys.
1. Chapter 1

**Title: **The Bad Guys Know It Too

**Summary: **Somebody from John's past is looking to settle an old score by going after Sam and Dean. Big mistake… Pre-Series. TeenChesters. Protective Big Bro! Dean. Hurt!Boys.

**Warning: **Rated T for bad language and descriptive violence. There will be sexual innuendos but NO sexual abuse.

**Disclaimer:** I don't own anything.

**Author's note: **Dean is 16, Sam is 12.

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_My strength and my weakness are twins in the same womb.  
-Marge Piercy-_

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**The Bad Guys Know It Too**

**Chapter 1**

"I hope you know that this is gonna cost you your fucking head, Jackie…"

Unperturbed by his partner's warning, Jack continued with the task at hand and snapped the cuffs closed around the dangling wrists of John Winchester's oldest son.

Straightening up from his crouch, he ignored the protesting pops and groans of his bones and gave the unconscious teenager in front of him a last once-over.

"Look at them…" he sighed, seemingly satisfied with the way Dean was hanging from his bonds, drugged and strapped securely to a chair, with nothing on his body but a battered T-shirt and his jeans after Jack had removed the small arsenal of weapons the kid had kept hidden beneath his baggy clothing.

His eyes wandered over to the other Winchester boy who was similarly tied to a chair, mirroring his brother's slack position, dark lashes fanned against ghostly skin and chocolate colored bangs hanging lifelessly into his face.

"All trussed up and helpless like that… It's kind of like holding John's pulsing heart in your fingers–"

A triumphant smile settled on Jack's lips, knowing the absolute truth behind the words and enjoying the little rush of power that surged through him at the realization.

For some reason the whole hunters' community seemed to have gotten it into its head that John freaking Winchester was a _legend_, an invincible knight in shining armor hacking and slaying his way through an army of monsters and never failing at the job.

But Jack knew better.

He had taken one look at the man and seen past his carefully sustained steel facade.

Because behind the cocky-bullshit-attitude, where John was at his most vulnerable, he wasn't the hero that everybody made him out to be- but he was merely a father, desperate to protect his sons from a world of darkness.

And Jack was going to use that against him.

"Well enjoy your power rush while it lasts…"Andrew cut in from the side, crossing his arms in front of his bulky chest. "Cause Winchester's gonna rip you apart for touching his boys when he finds you... "

"Oh is that so?" Jack inclined his head to the side, running calloused fingers over the cool metal of his Beretta.

He thought about it.

Thought about all the things he could do to these boys now that they were at his mercy.

Especially considering how protective the older one seemed to be of his younger sibling…

He thought about John's expression when he found the motel room empty and his rage afterwards, when he realized that the person behind his sons' disappearance was actually an old acquaintance with deadly intentions.

He thought about making these boys suffer and in doing so, putting their father through his own personal hell.

And then he smiled, a strange sense of serenity washing over him.

"He can try…" Jack said softly, before walking over to stand in front of Dean's slumped form. "But it won't end well for him."

He brought down the butt of his gun against the side of the teenager's face, reveling in the pained groan he elicited with his brutal waking attempt.

Blood gushed from where a tooth had nicked the boy's slack lips and Dean's head rocked back from the force of the blow.

"C'mon you little bastard…" he murmured under his breath, grabbing a fistful of short-cropped hair to keep the boy's head still. "Nap-time is over."

"Jack–"

"Shut up, Andrew! If you're gonna chicken out on me now, then get the fuck out of here. I can do this just fine without your sorry ass trying to appeal to my conscience–"

Without waiting for his partner's response, Jack tucked the gun back into his waistband before backhanding the blonde teenager squarely across his freckled cheeks.

The resounding echo of flesh hitting flesh reverberated through the walls of the basement and Jack gleefully watched the ghostly imprint of reddening skin from where his fingers had marked up the boy's face.

Girly eyelashes fluttered weakly as the teenager slowly came back to his senses, pupils moving rapidly beneath his closed lids.

"There we go, princess," Jack mocked with another swat at the boy's chin. "Open those shiny peepers…"

When he felt the kid's body tense and go rigid beneath him, breath getting more labored with each second, Jack knew that Dean had clawed his way through the thick veil of confusion his brain was swathed in.

He was awake.

And clever little bastard that he was, he pretended to still be out of it in order to buy himself a little more time and assess the situation.

Well what Dean didn't know yet, was that this was Jack's game… and they were gonna play by his rules.

Turning around to face Andrew who still looked uncomfortable after having watched Jack's display of violence, Jack's eyes narrowed in silent demand, urging his partner to play along with what he was going to do next.

"Seems like Dean isn't in the mood to chat–" he trailed off excessively, eyes slowly wandering from Andrew to where the younger of the two was still hanging listlessly in his bonds.

"How about we try to rouse little Sammy instead? I'm sure he'll be more cooperative…

It was all he needed to say to get the desired reaction.

The second the younger boy's name was spoken, Dean's eyes snapped open, still slightly unfocused from the drugs, but not enough to hide the evident panic in his gaze.

"No, don't!" he rasped. "Don't you freaking touch him!"

Jack could barely contain his glee.

It was just like he predicted.

Sam Winchester was his fucking golden ticket to both of the other Winchester men's destruction.

The cute, shaggy-haired kid with the bashful awkwardness and the dimpled smile was going to get Jack everything he wanted, because neither John nor Dean would be willing to risk the safety of their youngest and most vulnerable family member.

Just perfect.

"Who the hell are you?" Dean croaked, barely sparing Jack a glance before his frantic gaze latched onto his brother's unconscious form.

His practiced eyes ran over Sam's body appraisingly, scanning the kid for injuries, before finally- somewhat satisfied at finding his brother relatively unharmed- settling back on Jack.

"What did you give him?"

How Dean mustered enough energy to glower like that- Jack had no idea… Theoretically the teenager shouldn't even be talking after the tranquilizer shot he took to the neck not even three hours ago.

Blaming the boy's thick-skinned resilience on the typical Winchester stubbornness, Jack stepped out of the shadows and pulled his gun from the waistband of his jeans.

"Same thing I gave you. A mild sedative…" Jack explained with a slight shrug of his shoulders, as he stepped up behind the chair Sam was tied to. "Rohypnol to be exact…"

Oh, that got Dean's attention alright.

"Rohypno– you mean… r-roofies?" Dean repeated slowly, the last bit of confusion dissipating from his gaze.

Jack chuckled softly, looking down at Sam's mop of brown hair. "I guess that's another name for it, yes."

Eyes widening in horror, the teenager shot forward in his seat, tugging viciously at the cuffs that held him in place. "_You son of a bitch!_ You better not have touched a single hair on his scalp or I'll freaking _end_ you–"

Jack's heart fluttered in response to the wild protectiveness in Dean's voice and actions- having no doubt about the fact that the teenager would find a way to get loose and tear him from limb to limb if he had actually used the roofies for their intended purpose…

Not yet willing to put the frantic big brother out of his misery, Jack ran his fingers through the unconscious kid's brown locks in a mockery of affection, before grabbing a fistful of hair to lift Sam's face.

"_Get away from him or I swear to fucking god_–" Dean snarled and that was when Andrew stepped in from the side to spoil his fun.

"Calm the fuck down, kid. We didn't do anything to your brother, alright?" the plump man tried to soothe the enraged Winchester, raising both palms in a gesture of peaceful reassurance. "Didn't do anything to either of you for that matter…"

Jack rolled his eyes at his partner's indulgence.

"Now see, what my buddy's trying to say here, is that we didn't do anything to you, _yet_…" he corrected, lifting his gun to wipe a strand of hair from the boy's eyes almost lovingly.

Dean gritted his teeth, muscle ticking in his cheek.

The boy's face was so expressive- it was easy to read the torment about having to watch his helpless little brother getting fondled without being able to do anything against it.

"What do you want from us?"

See… now they were on negotiating terms.

"What I want from you…" Jack didn't try to hide his grin as he leveled the gun against Sam's temple, feeling the boy stir beneath his hands.

"Is absolute obedience. You do or say anything I don't like and- _boom_–"

He cocked his gun for theatric effect, watching gleefully as Dean's eyes went wild with terror, arms twisting fruitlessly behind his back.

"Don't!" he hissed, tugging viciously on his cuffs. "Let him go…"

The minute twitching of the younger boy would have been easily lost on inattentive eyes, but never on Dean- who had probably sensed the kid's impending awakening long before Jack had done so himself.

Sam made a low sound of protest, twisting slightly in Jack's grip as he tried to wriggle away from the sensation of cold steel against his skin.

Still too out of it for words, the kid grumbled something incomprehensible, arms twitching slightly beneath the too long sleeves of his loosely fitting hoodie.

"Jack, let him go…" Dean said imploringly, voice growing more frantic now that his brother was close to regaining consciousness. "Let him go, _please_–"

There was that magic word of broken compliance Jack had been waiting for.

Meeting Andrew's gaze over the shaggy haired boy in his grip, Jack shot him a look that said _'I told you so'_ before slowly lifting the gun from the kid's forehead and taking a step back.

"Wha–" the younger boy murmured drowsily, trying to raise heavy eyelids to a darkened world.

Dean leaned forward in his seat, bringing his body as close towards his brother's as physically possible.

"Sammy–" he said on a shaky exhale, features losing some of their tension and voice growing softer. "Sam, c'mon buddy… open your eyes."

"D'n?" Sam croaked out, licking his lips. Then the boy's arm suddenly twitched, movement painfully restricted by the metal that was wound around his wrists and his forehead creased into a frown."'s going on?"

Confusion was dripping heavily from the kid's voice as he tried to recall what had happened and couldn't come up with anything through the lingering effect of the drugs.

"'Y'okay?" Sam murmured sleepily and Dean broke out into a shaky laugh that bordered on hysteria, eyes glassy with tears as he shook his head.

"M'fine, kiddo. What about you, you feeling alright?"

Getting tired of the brother's exchange, Jack took a step forward and backhanded the kid across the face- just like he had done to Dean earlier.

Maybe this would speed things up a little.

They didn't have time for this shit.

The younger boy grunted in pain and shock, hair sailing through the air as his head was whipped forcefully to the side.

"Leave him alone, you fucking asshole! Get your fucking hands away from him–"

"Shut him up, Andrew," Jack snapped at the bulky man who hadn't proven himself worthy of this job in the slightest so far.

"Dean?" Sam whimpered in a pitiful tone, confusion and fear clearly audible in his words now that his vision cleared and the picture pieces finally fell into place.

His wide hazel eyes sluggishly tracked Jack's movement, scrawny frame flinching back in his seat at the intimidating pose the hunter struck.

"'s happening?"

The older Winchester was just about to answer, doubtlessly trying to reassure his little brother that he shouldn't be afraid… that Dean wouldn't let him get hurt, when Andrew stuffed a dirty rag into his mouth, effectively shutting him up.

"uhmgn–" the teenager's nostrils flared, eyes turning to liquid fire as he tried to dislodge the fabric from behind his teeth and found himself unable to do so.

Using the older brother's enforced idleness to his advantage, Jack pressed up into the Sam's personal space, breathing hot and wet against the trembling patch of skin on his neck.

"You wanna know what's going on, kid?"

Sam's lips trembled, looking up through glassy but lucid eyes as Jack tilted his chin to the side, forcing his gaze back onto his incapacitated brother.

"You see… your Daddy took something from me a long, long time ago and I intend to get it back from him. And you two are gonna help me with that, won't you?"

Sam blinked, visibly drawing strength from his brother's reassuring gaze, until Jack grabbed a fistful of his hair and yanked his face to the side, breaking the connection.

"I'm gonna need an answer to that question, kiddo…" Jack sneered into the kids face and then huffed in anger when Sam mulishly pressed his lips together, refusing to respond.

"That's not very nice of you, Sammy… I'm afraid I can't let that kind of insubordinate behavior slide…"

He snapped his fingers- jabbing a thumb towards Dean and Andrew hesitated for a second, before taking the wordless order and planting a fist into the older Winchester's stomach.

"No, Dean!" Sam cried out, jerking fruitlessly at the cuffs around his wrists and ankles as he listened to his brother's muffled grunt of anguish and watched him curl up on the chair across from him.

Andrew repeated the action, hitting Dean in the sternum, this time more forcefully until Sam whirled around to bestow Jack with a pleading, tearful look. "Stop it, don't hurt him!"

"Me?" Jack asked, feigning innocence. "I'm not the one hurting him… Sam. This is all on you, don't you see? If you had done what I wanted in the first place-"

"Alright, I get it! Just stop hurting him… _please_… "

Jack raised a palm, indicating for Andrew to stop and the sound of knuckles hitting flesh died down.

"There we go now, that's better…"

Then he dug his phone from his jeans pocket and held it out in front of Sam's face.

"I'm going to uncuff you now and you'll call your father for me like a good boy, got it?"

Sam pursed his lips, eyes sparking with silent defiance, even as he nodded his consent.

Dean groaned something incomprehensible into his gag, but it wasn't hard to figure out what the older brother was trying to say.

Jack could see the doubtful hesitation in the younger one's eyes at his older brother's disapproving grunts.

Apparently Dean didn't like the idea of getting their father involved in this.

Knowing he had to keep Sam in line, Jack pulled his gun and pointed it at Dean's writhing body, eliciting a shocked gasp from the frightened kid.

Mouthing a soundless _'No'_ in protest, Sam shook his head with wide, pleading eyes.

"You don't do what I say and he's dead."

Biting his lower lip, Sam sniffed miserably and nodded his understanding, willing to do anything if it meant his brother's life would be spared.

Satisfied with the kid's fearful obedience, Jack unlocked the cuffs and pressed his phone into Sam's shaking fingers.

"Dial," he urged with a grim expression, weapon never wavering from his aim.

Sam's fingers were shaking so bad he typed in the wrong digits three times before he got the number right.

It rang four times, before John finally picked up.

"D-dad?" Sam said shakily, eyes filling with tears when the familiar timbre rang from the other end of the line.

That was Jack's cue to step in.

Snitching the phone from the boy's sweaty fingers, Jack settled the earpiece between his head and shoulder.

"Hey there, Johnny… remember me?"

There was a pause, a barely-there sound of shock, before John responded.

"_Sampson?_" he rasped.

A lazy grin settled on Jack's lips at being recognized. "Good to hear your voice, Winchester… it's been a really long time."

"If you've hurt my son in any way, I swear to god you'll live to regret it, Jack-"

"Hate to tell it to you, John, but you're in no position to make threats," motioning towards Andrew yet again, Jack took a step closer to Dean.

"In fact, you're in no position to do anything but obey my orders if you don't want your boys to pay for your own stupidity-" he held out the phone just in time to capture the teenager's low grunt of pain when another punch hit his abdomen.

"NO! Dean! Stop it–" Sam thrashed against his cuffs furiously when Andrew continued beating his brother.

"_You fucking bastard! Leave them alone, you sonofabitch_-"

"Not sure I like your tone very much, there Johnny… but since you're so upset right now I'm willing to make an exception."

"What the fuck do you want from me?"

Jack smiled softly, dragging out the answer to prolong John's suffering. "I want my token back, Johnny. The one you took from me twenty years ago… remember?"

A tense silence spread between them.

Then John swore softly under his breath. "I don't have it anymore, Jack, just… god… it's been over two decades, why would you–"

_I don't have it anymore… don't have it anymore… don't have it..._

The words echoed through Jack's mind like a broken record, heart thundering wildly in his chest as a calm rage suddenly took hold of his body.

"What do you mean, _you don't have it_?!" he snapped, fingers tightening around the phone.

John's voice was strangely subdued when he responded. "Look… let's talk about this, alright? I'll get you a new one- a _better_ one… just… leave my sons out of this, alright?"

Nostrils flaring, Jack locked his jaw and closed his eyes, taking a deep breath.

"Now listen up, you goddamn asshole. You've got one day to get me my charm back. One fucking day. And for each one of these 24 hours, I'm gonna make your boys wish they had never been born… you take any longer than that? I'm gonna snap their freaking necks. Are we clear?"

"Jack, c'mon, don't you fucking do this–"

Losing his patience, Jack whipped around and grabbed Sam's free arm, before viciously twisting it behind the boy's back, causing his shoulder to pop out of its joint under the combination of his weight and momentum.

The kid's anguished scream put Jack's teeth on edge and set the older brother into an angry frenzy.

"You're fucking _dead_, Sampson. _YOU'RE DEAD, YOU HEAR ME?!_" John screamed on the other end of the line.

"You got 24 hours, John. Don't make me wait…"

With that, Jack snapped the phone closed, lifting his eyes to the ensuing chaos around him.

Time to get this party started.

**TBC...**

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_Hey guys! :) I am currently laid up in bed with the flu which leaves me with too much time on my hands- so here's a little side-project I started... Please tell me what you thought and if I should continue! Reviews make my day! :D_


	2. Chapter 2

**The Bad Guys Know It Too**

Chapter 2

**Warnings: **This chapter contains graphic descriptions of violence, bad language and a character death (not the boys).

**Author's note: **Dean is 16. Sam is 12.

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The kid was crying, and not in a pretty way either.

Tears of agony were running down his reddened cheeks as he tried to suck in air through his clenched teeth and snot was dripping from his nose.

Jack snorted in dismay and re-adjusted his grip on the teen's squirming limbs, before meeting Dean's stormy green eyes over Sam's tousled mop of hair.

If Jack hadn't already known that the older brother would do anything for the writhing and sobbing mess of a kid in his grip, he would have realized in the second he saw the desperation on Dean's face at having to watch his little brother in so much pain.

Twisting fruitlessly in his bindings, Dean was screaming into his gag, doubtlessly uttering deadly threats at Jack for having dared to put the youngest Winchester through this torture.

Jack figured John must have taken both his boys on several hunts before, which meant that they probably weren't unfamiliar to getting hurt or injured on a job.

It was par for the course- getting banged up came with the job description, no matter how much John might have tried to protect them.

He was willing to bet the older boy had taken a few good hits before and judging from the amount of sympathy in Dean's gaze, he most definitely knew the kind of pain that came from having your shoulder dislocated from personal experience.

Jack himself had always found that particular injury was a fabulous device for dramatic effect.

Not deadly. But extremely painful.

Restricting the enemy's mobility.

Quick and incapacitating.

Jack ran a finger over the kid's limp shoulder, brushing up against the disjointed bone until the boy cried out once more, louder this time, trying to twist away from his punishing hold.

"Hushh…" Jack whispered, never once taking his eyes from the enraged older boy who glared daggers at him from where he sat across from them. "It's okay, Sammy."

Dean's glower intensified tenfold when Jack used the kid's nickname in a mockery of a the loving gesture it was supposed to be.

The tension in the room grew and Jack smiled cruelly, watching the flicker of panic in the older boy's intense glare upon realizing what was about to happen.

Jack intended to snap the joint back in place. Or at least that seemed to be the conclusion the older Winchester had drawn from their tormentor's actions.

Dean went still in an instant and his eyes flashed over to Sam, before taking on a pleading quality.

He shook his head in a silent attempt to keep Jack from hurting his brother even further.

Sam tensed beneath Jack's hold, obviously taking his cue from his big brother's sudden shift in demeanor.

Andrew stepped in from the side. "Jack, maybe you shouldn't—"

"It's okay…" Jack said once more, cutting his partner off and reaching out to brush a hand against Sam's forehead, wiping wayward strands of hair from his brimming eyes.

He wanted Dean to have a clear view of his brother's face for what was about to happen.

Sam shuddered in his hold, lips quivering as he tried to get his pain under control. "Please …" he whimpered pitifully and Jack didn't really know what he was pleading for.

He didn't care either, not with the way Dean was reacting to the word, his face twisting into an angry sneer as his eyes sparked with silent fury at the way Jack had reduced his little brother to begging.

"Jack, I'm serious," Andrew stepped forward, blocking his sight of the livid teenager in his attempt to calm Jack down. "You've made your point, okay? John's already on his way, so there's no need to—"

"Get out of the way, Andrew_,_" Jack ordered, bristling with anger.

He should have known that Andrew would mess this up.

The guy had a son of his own, who must have been right around Sam's age now.

Jack should have known that the resemblance would be too big- that Andrew didn't have the guts to pull through with this, not while imagining it was his own kid getting tortured and therefore sympathizing with John's brats.

When Andrew hesitated to step aside, Jack rolled his eyes.

Pulling the gun from the back of his jeans, he pointed it at his partner and watched the guy's eyes widen in disbelief.

"Get. Out. Of my. Way," he repeated slowly, emphasizing each word as if Andrew was slow on the uptake- although, thinking about it, maybe he was.

"You won't shoot me…" Andrew muttered defiantly, holding his stance and squaring his shoulders. "You wouldn't dare."

"Like I said…" Jack sighed. "I don't need you to do this, so you either do what I say or you get a bullet through your skull. Both options are fine with me…"

"You're insane," Andrew whispered, even as his face grew more concerned and insecure by the second.

He took a half-step to the side, not far enough to reveal Dean's body.

"They are just kids, Jack. This is about their father, I thought we were clear on that. Ruffle them up a little to get back at John, sure. But what you're doing- it's unnecessary. And I won't stand for it…"

Oh you goddamned idiot… Jack suppressed the urge to slap Andrew up the head.

Because while the dumb son of a bitch had done nothing but messing up his plans so far, killing him sure as hell hadn't been Jack's intention. But now?

The guy just basically revealed his reluctance to participate in their little private torture session to John's kids.

And if Jack had pegged the two teenagers right, they were both mighty perceptive and clever for their age, which meant they would pick up on the obvious chink in Andrew's armor and try to get the man onto their side- make him turn on Jack to help them escape or something…

Especially the older one seemed to have a good way with words. There was no doubt in Jack's mind that Dean would be able to somehow convince Andrew to help them out if given the chance.

And even if he were to be careful, Jack couldn't risk that. Not with John on the loose and his token still missing.

Especially not now, when he had finally found the perfect leverage to bring John to heel.

So as unfortunate as it might be, Andrew had brought this onto himself.

"Well if you can't stand for it…" Jack shrugged his shoulders and pulled back the hammer of his gun. "Then you'll go down for it."

He didn't flinch at the sound of his gun firing.

Andrew's eyes widened and he had just enough time to gasp in shock and fear before the bullet lodged itself in the center of his forehead with deadly precision and he crumbled lifelessly to the ground.

Blood leaked steadily from the hole in the dead man's forehead as his life seeped from him and for the span of a brief moment, nobody dared to breathe in the confinements of the basement.

Jack felt the familiar rush of adrenaline that came from taking somebody's life and he took a second to close his eyes and take a deep breath, before the sound of screaming pulled him back to the present.

Oh right, the boys…

He should have known they wouldn't deal well with this.

Dean was thrashing in his bonds and screaming into his gag, his face and torso splattered with Andrew's blood as he stared down at the guy Jack had just felled in front of their eyes.

Judging from the shear amount of terror in his vibrant eyes, Jack was almost willing to bet the kid had never seen a human being getting killed before.

Ganking ghosts and werewolves, sure. With John as a father there probably wasn't a way around that.

But there was a distinct earth-shattering difference when it came to watching the life leave the eyes of a human being.

And the thought that he had been the one to bring this experience around, well it was a little exhilarating- Jack would admit that.

His eyes greedily flickered down to the other kid- the younger one, because if this was a new thing for Dean- Jack would have bet his ass that Sammy hadn't ever seen somebody die either.

He sure as hell wasn't disappointed.

For all their similarities, it was pretty obvious that John's boys couldn't be more different from each other.

There were obvious differences, like their age. But there were also more subtle ones, like the fact that Dean was clearly the more vocal one of the two- his preferred weapon was his sarcasm- a sharp tongue designed to enrage and distract his enemies.

A skill the boy had doubtlessly used to his advantage in plenty of occasions before and perfected over the years—which was also the reason why Jack had him gagged in the first place.

He wasn't easily prone to losing his composure, but with a guy like Dean- Jack wouldn't take any chances.

He was a threat that needed to be diminished quickly and efficiently.

With Sam, things were clearly easier.

The boy was so completely out of place in the hunter's community, Jack had been wondering when John would finally understand that he would never become the mindless killing machine his father was making him out to be.

He was obviously the dreamer in the family- eyes alit with a strange hopefulness that came from his yearning for a better life.

He clearly didn't want any of this- the constant moving, the hunting, the sword of Damocles hanging over their heads, threatening to fall down and snap their necks at any given opportunity.

The kid had been through a lot- and yet he was still so innocent- so fucking _pure_.

And Jack was delighted at taking some of this pureness away- at crushing the innocence beneath his thumb.

So when he looked down to find Sam with impossibly wide eyes, staring sightlessly and unblinkingly at the dead body of a man that used to be a living- walking and talking human being only seconds ago, he was barely able to contain his glee.

The boy's face was sickly pale, his whole frame was shuddering with the shock of what happened.

The only thing giving his panic away was the rapid rise-and-fall of his chest as he worked himself into a shocked frenzy.

"You know…" Jack spoke softly as he tucked his gun away and walked over to Andrew's corpse.

Stabbing his boot into the guy's side, Jack watched Andrew's dead body flop a little- satisfied with the typical boneless movement that came from zero brain activity.

"I don't like it when people call me insane. I prefer the term lunatic genius…"

He grinned up at Dean, who was blinking away tears of his own, desperate eyes glued onto his catatonic little brother and whole body tense with the need to go check the kid out- with the need to reassure and comfort- an urge to nurture that probably came from taking up the role of a parent on top of his role as a big brother after their mother died and their dad became distant and revenge-driven.

Jack liked that unnatural closeness between the boys- the tender side to the older boy's gruff exterior that was clearly reserved for his little brother and nobody else.

He also liked their silent way of communicating, liked to watch their meaningful glances- whole conversations flowing back and forth between them without a single word being uttered.

But right now, the secretive body language and word-less communication was put on hold for the terror of having witnessed Andrew's death and Jack decided that maybe it was time to give them a little break.

Straightening up, he walked over to Dean and ripped the gag out of his mouth with a vicious tug.

He stared down into the defiant teenager's murderous glower and held his gaze.

Crimson splotches of blood were splattered all over the boy's smooth features, standing out against the paleness of his skin like a colorful addition of the brown freckles that were gracing his cheeks and nose.

Glistening tear tracks were tracking clear paths against his skin from where the salty pearls had broken free from his eyes and his breathing was going heavy, heart matching his little brother's erratic pulse from where he said across from them.

"Let me take care of Sam…" the blonde boy rasped, voice hoarse from screaming so much.

No sarcasm. No threats.

Just a simple request.

Jack glanced back over his shoulder to where Sam sat still unresponsive; sucking in breath after breath greedily –almost as if it was the only thing he still knew how to do.

Kid was probably about two minutes away from hyperventilating. And the older brother knew it.

Jack looked back at Dean with a suggestive smile.

"Tell you what-" he breathed out, low enough for the words to stay between the two of them. "You do something for me and I will let you be the one to relocate the shoulder instead of me doing it. Sound like a deal?"

Dean's eyes were flashing with anger and he looked about ready to jump Jack's throat and tear it out with his teeth.

Because the choice Jack had given the big brother was a tough one.

He could either stay tied to his chair and watch while Jack put the younger boy through even more pain or he could get up and be the one to inflict the pain on his own brother despite his already weakened and terrified state.

Neither of which was a very likeable option.

But even so, Jack knew what Dean's answer would be. Had known so even before he uttered his suggestion.

"What do you want me to do?" Dean pressed out between clenched teeth.

Jack clicked his tongue, eyes brilliant with a thrill of anticipation.

"For starters I want you to help me get rid of dear old Andrew here, before he starts stinking up the place…" Jack explained slowly, jostling the pile of lifeless meat on the ground once again with his booted foot.

Dean's nostrils flared at the irreverent treatment of what was used to be Jack's hunting partner, eyes flickering down to the corpse before snapping up at Jack.

"What else?" he demanded, eyes narrowing suspiciously.

Jack smiled at the reaction- having already suspected that there was much more to John's oldest than met the eye.

The kid was perceptive and quick-witted, capable of putting together facts at inhuman speed. He probably also had a good comprehension of human nature, which lead him to a natural suspiciousness.

Letting his eyes trail suggestively down Dean's body Jack's chapped lips twitched into a wicked grin. "What else are you willing to offer?"

There was a beat of silence. Then Dean's eyes widened with outrage.

"Oh you gotta be kidding me, you sick, twisted fuck," Dean spit back menacingly, visibly recoiling at the suggestion.

His eyes automatically sought out his little brother's form again before resettling on Jack, plush lips twisting with insecurity and disgust.

But there was no real hesitancy to him, no real decline of the offer.

Because deep down, Dean knew that there was nothing he wouldn't do to help his brother, or keep him safe.

And Jack knew it too.

"What do you want?" Dean growled out under his breath; face pinched and withdrawn, body fidgeting in his seat under Jack's appraising leer.

"Oh I will think of something for sure… How about you take care of that brother of yours before we do anything else, huh?"

Dean pressed his lips together and nodded, not meeting Jack's gaze.

"Just don't try anything, cause I would hate to have to hurt Sammy for your disobediance…" Jack trailed off as he kneeled down and unlocked the cuffs on Dean's wrists.

The teenager let out a breath when the ungiving metal was removed from his chafed wrists. He started to rub the abused skin on his arms just as Jack leaned lower to remove the second pair of cuffs from around his ankles.

When the boy tensed, Jack's eyes snapped up to bestow Dean with a warning glare.

"Try anything and you're dead," he said once again. "I only need one of you to get John to bring me my charm back and believe me when I say you don't want to know what I have in store for little Sammy over there, when you're no longer around to protect him."

Dean visibly deflated at the words, eyes shining with fear at the implied threat towards his brother.

"He's just a kid, you fucking bastard," Dean muttered in anger, features grimacing."Whatever you think you need to do to keep my father in line, you do it to me, understand? You leave him out of this."

Jack chuckled at that, turning the little key until the cuffs snapped open and stowing them away in his jeans pocket. Then he pulled his gun from his waistband and gestured towards the shaking kid on the other seat with its barrel.

"You don't get to tell me what I get to do or don't get to do, Dean. In fact, it's pretty much the other way around. Now your father messed up big time, and you two will repay me for that until he gets me my charm back. And whether it's with your blood or…" He let his eyes wander up and down the boy's body appreciatively, causing him to shudder. "…or payment of a different kind… that's for me to decide and for you to find out."

Dean swallowed convulsively, his gaze purposefully averted, even as his body tensed and twisted uncomfortably under Jack's stare.

"Go on," Jack urged silently. "Get over to your brother and get him to calm the fuck down. Put his shoulder back in place and then you'll help me with Andrew. Try anything and me and Sammy are going to tango …"

Dean shot him an unmistakable glower that promised a slow and gruesome death if his brother was to be harmed, before he pushed out of his seat and deftly outmaneuvered Andrew's lifeless body on the ground.

He sank into a crouch before his little brother and reached out towards the frightened boy with shaking fingers. "Hey Sammy…" his voice was soft and gentle, never intended to be heard by anyone else but the panicked kid.

Sam just continued to stare at the dead body, unable to register anything that was happening around him through the mind-numbing after-effects of his shock.

"Hey, don't do this kiddo, c'mon—" Dean implored, his voice cracking slightly as he cupped his brother's cheek and brushed a thumb against his pallid skin. "Eyes on me, Sam. C'mon let me see these shiny peepers. It's okay… you're gonna be fine. I promise… Look at me, _please_."

Jack sighed. "Make it snappy, Dean. We ain't got forever."

Dean didn't dignify the command with a response, his whole world narrowed down to the task of getting his brother to snap out of his shock-induced rigor. "Sammy… I know you're scared, but I need you to look at me. _Please, just—_"

"Dean." The boy's breath caught in his throat when Sam's distant eyes suddenly refocused on him, the glassy shimmer of tears intensifying until a first teardrop spilt from his eyes and he blinked.

Just like that the dam was broken and the boy started shaking, chest heaving with sobs as he sagged forward into his big brother's hold, burying his face in the nape of the older boy's neck like a puzzle piece falling into place.

"Hey, hey, calm down, kiddo… I promise it's gonna be alright, okay? Dad's on his way… we'll get through this. Just like we always do, huh?"

Getting impatient, Jack kicked over the stool Dean had been sitting on, satisfied with the way Sam flinched in fear at the loud clatter of wood crashing against the cemented floor.

"Get his fucking shoulder fixed,_ now_, or I will. Got it?"

"Give me a fucking moment to take care of him you heartless bastard- can't you see he's terrified?!" Dean shot back with so much defiance that even Jack was thrown for a second.

Oh this kid's protective streak was fierce...

And it was way stronger than his will to survive their current ordeal.

"You said we had a deal, remember? Now be a fucking man of your word and hold your end of it before I get to hold mine, alright?"

Jack pursed his lips, frowning slightly and not saying anything in response. Like he said- the kid knew his way around words.

False pride wasn't necessarily something Jack clung to- but the way Dean had phrased his sentence was an obvious attempt to appeal to it and Jack was kind of impressed by the tactics the teenager tried to apply on him.

So instead of shooting him for the audacity to try and trick him, Jack stood back and watched the scene unfold.

The younger boy clung to the older one for all he was worth, all the while sobbing incomprehensible nonsense into Dean's neck, while big brother kept reassuring and comforting the shuddering kid in his protective hold.

"_H-he's dead…De-ean he just die-died—ohgod…"_

"_Shhh… I know… I know kiddo…let it all out."_

The words were spoken in low, hushed voices, but Jack understood them all the same.

After a while, when Sam had calmed enough to catch his breath and meet his brother's gaze again, he was being pressed back and eased out of the embrace by Dean.

They exchanged a long and meaningful look - before Sam took a shuddering inhale of air, visibly steeling himself for what was about to come.

Dean gave his little brother a tormented look filled with obvious remorse. "You know I don't have a choice, here, right?"

Sam bit his lower lip and nodded. "It's okay. I-I'm glad you're the one doing it... Th-thanks—"

"Hey, don't okay? Don't thank me for this," Dean croaked, shaking his head before getting up from the ground and taking up a position beside his brother.

Sam looked up at him, trust and love shining from his tearful gaze, even as Dean's gentle palms settled on his arm and shoulder. "On three, okay?"

Sam gave him a watery attempt of a smile, before nodding curtly and closing his eyes.

"One-"

Dean grimaced as he looked down at his little brother's trembling body, unwilling to cause the kid more pain.

"Two-"

Jack saw the exact moment when Dean's reluctance turned into resolution, having no other choice but to obey their tormentor's orders and deftly snapping the joint back into place.

Sam's eyes flew open as he howled in pain and Dean instantly shot forward to wrap his arms around the boy's writhing torso and keep him from hurting himself even more as he continued to twist and squirm in agony.

"It's okay, it's okay. It's over, Sammy," Dean whispered against the boy's ear, hugging him to his chest from the side. "It's done. You're fine…"

Jack clapped his hands for theatric effect at the display in front of him, smiling crookedly at the two teenagers. "How sweet…"

"Shut the hell up, you psycho," Dean snarled in response, visibly shaken from his brother's torment as he suffered vicariously with the kid.

"You know Dean, I would watch my tone if I was you. Especially since your end of our deal is still open."

Sam turned questioning eyes onto his brother, concern etched into his young features despite the pain he had just been put through.

"What deal?" he asked. "Dean, what is he talking about?"

"Nothing," Dean gave back softly, clearly not wanting his brother to worry about that on top of everything else.

Jack had no such restraints.

"The deal where he promised me a return service if I let him tend to you," Jack explained slowly, dragging the sentence out until Sam's face displayed the shock that came with the implied threat in his sentence.

"No, Dean? What did you promise him? What's going on?"

How endearing… the kid was no less concerned for his big brother than vice versa.

These two had so many buttons to push.

"Don't worry about it okay, whatever it is- I will handle it—" the older brother tried to assure, even though the look on his face didn't hold the same confidence his voice did.

Jack smiled at them. "C'mon now, Dean. Enough big talk. You're a _man of your word,_ after all, aren't you?"

The muscle in Dean's jaw ticked as he clenched his teeth. "Let's get this over with, you son of a bitch."

Jack snickered softly at the snarky response. "If you say so…"

**TBC...**

* * *

_So sorry for the long wait, guys! I was in Barcelona for a week to regain some energy :) It's an amazing city, btw- if you ever get the chance to check it out, I can only recommend it. As for this story... I am kind of insecure if this chapter turned out alright. It's kind of hard to get back into the writing mode after a longer break. I want to thank you all for the amazing feedback so far! As per usual I am not really sure where I am going with this... but I think my main angle with this story is Jack's craziness and how he's toying with the boys and using them against each other... What can I say? I love them when they're all hurt and protective. Also, this story won't contain sexual abuse- despite the innuendos. Like I said... Jack is playing with them. Trying to figure out what makes them tick. _  
_So please, as always- drop me a note, let me know what you thought! Reviews make my day :D_


	3. Chapter 3

**The Bad Guys Know It Too**

**Chapter 3**

**Warning: **Rated T for graphic descriptions of violence and bad language.

* * *

Jack licked his lips, enjoying the wet drag of his tongue against chapped skin as he watched John's oldest son sink to the ground beside Andrew's lifeless body.

The teen's face was pale, mouth curled in disgust as he hesitantly reached out to wrap trembling fingers around one of Andrew's slack limbs, trying to get enough leverage to hoist the beefy corpse up into a better position.

"It's not going to work that way…" Jack chuckled amusedly, eyes tracking lazily over the bunching muscle beneath Dean's sweaty T-shirt.

The teen was definitely in a good shape, doubtlessly sporting more thews than other kids around his age usually did and Jack had no doubt that John was putting both of these boys through quite the boot camp training in order to have them agile and capable of defending themselves.

Unfortunately it took a little more than being muscular to move 230 pounds of dead weight across the room. Getting rid of corpses was a bitch that way; Jack had always found that particular part of the job especially annoying. Thank god he had someone to do the dirty work for him this time.

And it was more than just that, because while Jack certainly enjoyed not having to take care of Andrew himself, he took even greater pleasure from the way Dean's face scrunched up in disgust and horror every time Andrew's head flopped forward against the teen's chest or shoulder, accidentally smearing him with more blood.

Dean struggled to get the unresponsive pile of meat into the black body bag Jack had handed the teen earlier. But Andrew- stubborn bastard that he was- didn't budge from his spot on the ground.

"Told you this wouldn't work…" Jack uttered gleefully while keeping a threatening arm wrapped around the younger boy's chest at the same time. Restricting, but not cutting off air supply… just a friendly reminder about what was going to happen if Dean decided to do something stupid.

Insurance, if you wanted.

Dean stubbornly tried to lift Andrew's body up again, but only managed to drag the corpse a few centimeters to the side before it slipped from his grasp again and dropped to the ground. Huffing out a breath, the teen wiped a hand across his sweat slick face, cheeks flushed from physical exertion.

Brushing his thumb up lovingly over Sam's Adam's apple, Jack smiled at the way the floppy-haired kid's breath hitched in fear. Trying to wriggle out of his forceful hold, Sam made a small sound of discomfort, causing Dean to look up from Andrew and over at where Jack had his arms wrapped around his little brother's chest and throat.

"Get the fuck off him, you son of a bitch. That wasn't part of our deal."

Jack snorted. "Yeah well, neither was you trying to slow dance with Andrew… I told you to fucking_ bag_ the guy, not cuddle with him, Dean."

"_Bite me_," the boy shot back in a fierce whisper and Jack clicked his tongue disapprovingly at the snarky retort.

Jack had been willing to play nice with John's boys- really he had, but apparently the conventional methods didn't seem to work on John's oldest.

Clearly, Dean needed a little reminder of who was calling the shots here.

"Alright… you know what?" The hunter grabbed a fistful of Sam's hair and harshly jerked his head back, eliciting a pained whimper from the boy. "Let's spice this whole thing up a little, shall we?"

"_Dean_—" Sam whimpered, causing the older Winchester boy to shoot forward in a gut-reaction of motherly protectiveness.

"Nuh-uh-uh…" Jack softly chided, tightening his choke hold on the kid's throat until Sam started gasping for breath and thrashing around in his hold. "One more step and I'm gonna snap his neck, understand?"

Dean instantly stilled his movements.

"I asked if you understood, Dean," Jack prodded with another forceful jostle to Sam's throat. The kid started gagging, tugging desperately on his cuffs in an effort to free himself and if looks could kill, Jack would have been freaking annihilated by the one Dean bestowed on him.

"I _understand_, I fucking understand, okay? Now let him go!"

"Fair enough," Jack relented with a smug smile, releasing the squirming boy from his strangle hold. Sam started coughing and gasping for air the second he was let go, hair falling into his face as he tried to catch his breath.

"Now what do you say we play a little game to help you get done with dear ole' Andrew over there, huh?" Jack suggested with a playful wiggle of his eyebrows, snatching a piece of discarded rope from the dirty floor beneath Sam's chair. "I think with the right kind of motivation, you should be done with your task in no time…"

Dean's plush mouth thinned out into an angry, narrow line, eyes sparking with fury, but he was wise enough not to actually voice the '_go screw yourself' _that must have been on the tip of his tongue in that moment.

Progress. This was progress.

Jack would count every small thing a success with somebody as mulish as Dean.

"I don't need motivation," Dean pressed out, obviously having realized that whatever Jack was planning to do couldn't be anything good. The boy's emerald orbs flashed with a hint of panic when he took in the long cord in Jack's hands and his whole body was tense- waiting for Jack to let his guard down so that Dean would have an chance to make a move.

It wouldn't come to that, though. Not if Jack had a say in the matter.

Cause maybe he wasn't quite as ripped as the teenager in front of him- and neither did he have the kind of combat training John had put both of his boys through, but what he lacked in battle skills, he more than made up for in shrewdness and stealth.

And Jack wasn't afraid to play dirty.

In fact, he _loved_ to do just that.

Because these boys in front of him might be John's perfect little soldiers, clever and astute, trained and lethal… but they had one big Achilles Heel, namely each other.

Which meant as long as Jack had one of them threatened the other one would bow to his every whim.

It was freaking exhilarating.

"You ever been sailing before, boys?" Jack trailed off slowly, a dark grin of anticipation settling on his lips as he wrapped the loose end of the rope around his lower arm, holding the other end in his free hand.

Sam looked at him from behind a curtain of sweaty bangs, eyes shimmering with fear, as he took in the coarse rope in Jack's hands. The kid was smart. Jack figured Sam had already realized that this next part was going to involve him in some way.

And it terrified him.

Good.

Dean seemed to have drawn the same conclusion, his eyes turning wide with a dark sense of foreboding. "You said you'd leave him out of this Jack… if I did what you wanted- you said—"

"Well you _haven't_ done what I wanted, have you now, Dean? Seems to me that you're in need of a little extra incentive to get the job done. "

The boy shook his head, dread settling in his guts. "No. No I can do it, just give me a few more minutes and I'll have him in the damn' bag, but leave Sammy out of this, okay?"

A muscle in Dean's cheek ticked as he locked his jaw. "Please, Jack…" he uttered in a raw voice, obviously tormented by the mere thought that Jack could somehow hurt his little brother.

Ignoring the older boy's pathetic begging, Jack formed a loop in the end of the rope and tucked the bight on the other end through it, tightening it with a sharp pull.

"Can you tell me the difference between a noose and a loop?"

Probably sensing a way out of his predicament, Dean thought complying with whatever Jack wanted was the best way to avoid further suffering for his little brother.

"A noose tightens when you tug on it," Dean explained tightly. "The loop won't."

"Thatta boy," Jack grinned, repeating the motion from earlier until the rope had tightened into a knot. Then he stepped over Sam's chair once again letting the rope dangle in front of the boy's face.

"Jack **don't**…" Dean choked out miserably, shaking his head. "I'll take care of Andrew and whatever else you want me to do—"

Still smiling, Jack wrapped the sling around Sam's head, feeling the boy go rigid in the seat beneath him. A minute whimper of fear escaped the boy's lips at the feeling of the coarse rope against the vulnerable patch of skin around his throat, when Jack tugged the rope closed around Sam's gorge.

"Don't—" the shaggy-haired kid pleaded, craning his neck to the side to try and loosen the strain around his throat, but of course, the boy's wriggling did nothing to ease the pull of the rope.

"A grown man can last about 3 to 4 minutes without air when he's not struggling," Jack trailed off almost disinterestedly , gripping the base of the knot with one hand and the end of the rope with the other.

"A boy his age…" Jack smacked his lips together, fake-contemplating his options. "I'd say he's got about half of that- and that's if he keeps nice and still."

"No, please—" Sam shook his head, tears pooling in his frightened eyes. "Don't do this—"

Jack leaned down, gently thumbing away brown tufts of hair and breathing against the boy's ear.

"You ever play hangman before, Sammy-boy?"

The kid tensed at the whispered words, the meaning behind them as evident as the sun. Jack's lips spread into a slow smile when the kid shook his head in a silent plea for mercy.

"No?" Jack asked in mock disbelief. "Well you gotta try it then… it's a fun game… I'm sure you'll have a blast."

"Jack don't you freaking touch him, I fucking mean it," Dean snarled from where he was standing with balled fists, whole body coiled tight with tension at having to watch his little brother suffer.

It probably would have been easy for Dean to jump him, but with Sammy's life on the line and the threat of Jack snapping the boy's neck before Dean got a real chance to attack him, the teenager apparently was clever enough not to attempt anything.

"You know…" Looking up to meet Dean's panicked gaze Jack made a show of slowly pulling at the end of the rope, closing the noose around Sam's neck. "You could have done what I told you to and little Sammy here wouldn't have to find out about what it feels like to have every single bit of oxygen squeezed out of your lungs…"

"He's just a freaking kid, you sick bastard!" Dean's voice was filled with anguish, his whole frame shaking. Logically, he must have realized that there was no way he could maneuver Andrew's corpse over into that bag in less than 2 minutes, so he tried to make Jack cave with his words- plead for his brother's life.

Bargain.

But Jack didn't budge, pulling the noose tighter still and causing the writhing kid to choke and gasp as his airways were completely shut off, the rope digging painfully into his esophagus.

"You're right Dean, that's why I wouldn't waste any more time in getting to work if I was you. Like I said… he's got maybe one minute left before his system shuts off completely,… lungs seizing to work properly… heart rate slowing down… eyes falling closed…"

Jack watched in sinful delight as his cruel descriptions painted horrifying pictures in Dean's mind; the teenager's mind conjuring up images of his brother's lax body shutting down— suffocating.

There was a flash second of understanding in the older boy's eyes- barely there and then gone- where Jack could see panic turn into indestructible resolve and that's when Dean whirled around, dropping to the ground and getting to work with an astounding speed and deftness to his moves that hadn't been there before.

He grunted from the strain of pulling Andrew up, but this time instead of letting the corpse slip from his sweaty grip again, Dean purposefully propped the lifeless body up against his own chest and readjusted his iron grip on Andrew's slack limbs, before hoisting the dead man over to the body bag.

Jack was mildly impressed by the kid's stamina and pulled the noose tighter, wringing a choked grunt from Sam's gasping mouth in hopes to startle Dean into a reaction.

"Gotta go faster than that, Dean-o. Sammy's turning a little pale over here…"

But Dean was unperturbed; his whole face closed off in concentration as he continued to cross Andrew's unresponsive arms before his chest and deftly tucked the body bag up around the man's limbs.

It almost seemed as if he had completely shut himself off from the world, mind and body solely focused on the one task and nothing else.

Sam's struggling grew more frantic, his mouth falling open as he rang for air, precious seconds ticking by while Dean frantically rushed to save his brother's life.

And then it was over, Dean nearly tumbling to the ground after successfully having tucked Andrew's body away in the bag and having zipped it up to cover the corpse with the black tarp. His whole frame was shaking, chest rising and falling rapidly with panic as he straightened up on wobbly legs and sent Jack the most piercing glare he could muster.

"Let. Him. Go…" the teen demanded in a murderously low voice, verdant eyes flashing with the unmistakable promise of revenge for what Jack had just put them both through.

Sam's struggles were getting weaker with each passing second, his choking gasps growing more desperate and lips turning a light shade of violet.

"I said let him go!" Dean burst out angrily, his voice thundering through the basement. "Let him go right this second or so help me god, I will freaking _end_ you, Jack."

Jack had to chuckle at the fierce display of protectiveness… This boy was like a simmering volcano, ready to spit fire. He definitely was on the verge of the breakdown right then, but Jack didn't let go of the rope in his fists, didn't relent his hold or ease off the pressure he put on the kid's throat.

Two minutes must have long passed by now, but Sam was still living, still fighting.

Maybe he had underestimated the kid at first. Maybe Sam had a lot more strength in him than Jack had first suspected.

"Dean, Dean, Dean…" Jack sighed teasingly, meeting the teen's murderous glower. "You're all talk and no action—"

"That enough action for you, you fucking bastard?!" It happened so fast, Jack had trouble catching up with it. He thought he imagined it at first- because he had been _right there_ the whole freaking time, watching the goddamn' kid's every move- but all of a sudden Dean pulled a gun from his jeans, pointing it at Jack in a swift move.

There was no fear or hesitation in Dean's gaze when he cocked the hammer, only anger and deadly resolution.

"You let your captives bag up your _buddy_ without frisking him first, you stupid idiot? Let my brother go or you'll get a hole between the eyes to match your freaking fellow's over there…"

Jack swallowed back a burst of anger for his own stupidity.

Andrew had been such an idiot from the start that Jack hadn't even thought of him carrying weapons, much less an automatic.

But he should have checked! Of course, he should have fucking checked the body before letting Dean get anywhere close.

He had gotten a little carried away with the bittersweet feeling of power at slowly squeezing the life out of John's youngest.

But he had watched Dean's every move, making sure he didn't try anything, so how could Dean finding a firearm have so completely slipped his attention?

"LET HIM GO!" the blonde teenager beckoned, taking a threatening step forward.

If the kid had any intention to shoot Jack, he would have probably done so already, but there was a hesitation to him- a moral dispute inside his mind about killing a human, that could work to Jack's advantage if he played his cards right.

"C'mon, Dean…" Jack drawled out slowly, feeling Sam go weak and sluggish beneath him, body twitching almost spasmically now that the life was leaving him.

"You seriously think I'd give Andrew a loaded gun when I was planning to off him later? I mean go ahead and take a shot at me if you want- but this baby's full of blanks and you know it..."

He ended his argument on a small vindictive laugh and applauded to himself for being such a damn' good actor.

Dean looked insecure, his eyes filled with tears at the way Sam's body had stopped fighting, limbs twitching slightly as they limply fell to the side and Jack knew an opportunity when he saw one.

"Drop the gun, Dean. He doesn't have much fight left in him now..."

"You're bluffing," Dean hissed, shaking his head.

"Maybe I am- maybe I ain't..." Jack shrugged his shoulders. "But are you willing to risk it when your brother's life is on the line?"

Jack breathed an internal sigh of relief when the teenager hesitantly lowered the weapon and dropped it to the ground, face grimacing with anguish as he turned a wide-eyed, broken-hearted stare at their tormentor. "Please… just whatever else you want from me, you got it. But let him go…"

"Whatever I want from you, huh?" Jack repeated slowly, rolling the words on his tongue suggestively.

Dean looked defiant, eyes glued desperately to his suffocating little brother, but he nodded nonetheless, lips pressed together and vocal cords bunched up with tension.

"Yeah… god, whatever the hell you want. I swear. Just let my brother go, you fucking bastard."

And then Jack stepped back, releasing his strangling hold on Sam and easing the noose from around the kid's neck.

Sam lifelessly sagged forward in his bonds, not gasping for air like any suffocating person should be after having been bereft of oxygen for so long. He just slumped in his seat, mouth hanging open and eyes closed.

For a second nobody moved and Jack was almost willing to bet that he had gone too far and killed the boy for good.

Dean seemed to come to the same conclusion, because the next second the teenager was a sobbing babbling mess, grasping and clawing at his little brother's body and babbling nonsense into the kid's messy hair as he cradled him close.

His sluggish hands found Sam's pulse point beneath the angry red strangle marks on the kid's throat and a broken sob of relief rushed from Dean's lips at finding a weak heartbeat throbbing against his fingertips.

"Oh gawd… oh fuck—Sammy, don't you do this…Please—" the teen cried and then turned to shoot Jack a piercing glower over his shoulder. "Fucking uncuff him before it's too late, you son of a bitch!"

Uncuff him? Jack looked puzzled for a second before catching up with the frantic teenager's trail of thought… Right. Sam was still alive but not breathing. Which meant someone else needed to do the breathing for him.

Huh. Jack hadn't even thought of that, already seeing the kid as yet another victim to fall under the collateral damage sector in his list of killings. But then he finally understood what Dean wanted from him.

He kicked over the stool Sam was bound to, knocking it to the ground along with the kid. "There you go, slugger. All set up for your little CPR session. I'll even cheer you on if you want me to."

He knew he was pushing it, but what could he say? Being evil was fun.

Dean sent him the most hateful glare Jack had ever received (and that was saying something) before leaning over his shackled brother and starting the chest compressions.

With the way Sam's arm was still cuffed to the backrest of the chair, the extra weight of Dean on top of the kid's torso was pressing the ungiving metal further into his bound wrist, but a broken hand was nothing in comparison to Sam dying and Dean seemed to come to that same understanding as he started resuscitating Sam's blood circulation with vicious chest compression.

"_C'mon, c'mon…don't you freaking dare—_"

Taking a deep breath, Dean tilted his brother's head back, pinching his nose shut with thumb and forefinger and then leaning down to seal their mouths.

From the looks of it Dean had done this before; his moves were sure and practiced, his face determined as he leaned back to continue pumping his palms against the younger boy's chest.

"_Breathe, damnit!_"

Jack wasn't a medical expert but if he had to guess why the kid was unresponsive, he'd say the boy's airways had collapsed during the strangulation. Usually this would require instant medical attention, but it wasn't exactly like Jack could or _would_ call an ambulance to save the kid.

"God….Sammy…" Dean choked out, tears running down his cheeks as he desperately gave on live-spending oxygen to his brother, trying to keep the kid alive.

"_Please_… just—"

Dean's broken pleading was harshly interrupted by Sam's coughing as he finally started to react to the CPR and regained his consciousness. The kid tried to take a shaky breath of his own and failed miserably at the attempt when his swollen airways protested, causing him to writhe and groan in protest, mouth opening and closing like a stranded fish trying to get back into the ocean.

"Oh thank god—" Dean blurted out, shoulders slumping with relief and eyes overflowing with tears of fear over almost having lost the most precious thing in the world to Jack's senseless cruelty.

"You're okay… you're fine, I got'cha…" Dean muttered brokenly against his brother's mop of hair, as he cradled the gasping kid as close against his chest as possible with Sam still being stuck in that goddamn' chair.

Sam whimpered in response to his brother's calming words, wheezing for breath and growing more desperate by the second when he couldn't force enough oxygen into his lungs.

"Slow… take it easy, your throat is swollen, Sammy… you gotta calm down, kiddo."

The gentle stream of reassurances seemed to have the desired effect on the kid when the boy's panicked attempts to suck in air through his abused esophagus slowed down into a more or less normal breathing pattern.

"There you go, buddy… that's it… you're doing good."

The easy transition from lethal hunter to overbearing, protective big brother was seamless and even though Jack was sure that this was his cue to break up the loving display, he found himself staring at the gentle exchange between these brothers instead- watching the way they drew comfort from each other even in a seemingly unbearable situation. It was fascinating, the way Sam seemed to react to Dean's voice and touch- the way the kid instantly calmed at his big brother's words, even though he was barely with it enough to be breathing.

And Dean… well the boy certainly loved that kid with a ferocity that would put even parents to shame. If that hadn't been absolutely clear from the beginning, it would have been evident in the way the older brother looked down at Sam with a watery smile on trembling lips, gently stroking the boy's heaving chest with one hand while cupping his chin tenderly with his other.

"_De'…_" the younger boy rasped and then started coughing again from the strain of trying to speak.

"Hey, shhh… none of that," Dean shushed softly, rubbing his thumb across the boy's jawline. "Don't try to talk, alright? You need to focus on breathing now…"

Sam grimaced, his cheeks slick with tears as he continued to struggle for breath through his swollen throat. "_Hurts_…" he croaked out, squeezing his eyes shut against a wave of pain.

Dean inched closer from the side, wiping a stray tear from his brother's glistening cheeks. "I know… I'm so sorry Sammy… _god_, I thought I'd lost you there for a second—"

Sam sniffled miserably, shamelessly leaning into his brother's touch and drawing comfort from Dean where it was offered so freely.

The kid tried to swallow and ended up gagging instead, which once more lead to a round of rough coughing. And that's when Dean finally seemed to remember that they weren't alone in the room, sending a pointed glare over his shoulder without really turning around to face Jack.

"He needs water," the blonde teenager informed curtly, his face holding none of the loving, reassuring tenderness Dean had shown his little brother only seconds ago.

Jack shrugged his shoulders. "So?" he asked in a monotonous voice, walking over to pick up Andrew's gun from where Dean had dropped it earlier.

"I need a foot massage and a nap. Looks like neither of us is gonna get what they're looking for…"

Dean´s glower intensified and he straightened up from the ground, eliciting a soft protesting sound of vulnerable confusion from his younger brother who seemed to have a hard time following their conversation.

The teen gently patted Sam's chest in reassurance before carefully lifting the chair up again, heaving Sam into an upright position and softly apologizing when his brother's arm was jarred at the movement. "Is it broken?" Dean wanted to know, gently prodding his brother's cuffed wrist from where it was hanging limply in the steel restraints. "Blink once for yes, twice for no."

Sam blinked twice, but the shimmer of tears in his eyes gave his pain away. Maybe his hand wasn't broken, but the wrist had to be sprained at least after having taken the brunt of his body weight when the stool was knocked over. And a sprain usually hurt even more than having your bones broken.

Dean sighed, having probably come to the same conclusion before gently moving to Sam's front and running practiced hands along the kid's torso. "How about here? Did I get any of them nicked or broken? Can you breathe normally apart from your swollen throat?"

Sam looked confused for a second, blinking a couple of times before swallowing weakly and opening his mouth for a response.

Then Dean seemed to notice his mistake and quickly halted his brother's attempt to talk. "Fuck, I'm sorry. Too many questions at once, huh?"

The kid still looked a little confused, but he blinked nonetheless, playing along with his brother's game and answering each of Dean's questions dutifully.

Jack was mesmerized by the way these boys communicated, effortlessly understanding each other without a single word being uttered, almost like identical twins or psychics. He had already suspected for these two to be close but what he was witnessing here was far more than he had ever given Winchester's sons credit for.

Taking a deep breath, Jack rubbed his jaw and inclined his head to the side. "Say I'd find it in myself to bring him some water and ice to get that swelling down…"

Dean's back tensed, his careful examination of Sam's ribcage intermitted as he shot Jack another questioning look.

"Get to the fucking point," Dean snapped having apparently ran out of patience. "What do you want?"

"I want you to give Daddy dearest a call… it's about time we got in contact again, don't you think? He's kind of missing out on all the fun we're having…"

Jack pulled the magazine from Andrew's gun before snapping it back and flicking the hammer to cock the gun. Dean's eyes widened slightly in realization, but before the teen could say or do anything, Jack aimed the loaded MP-40 at his head and broke out into a toothy smile.

"It was real fucking stupid of you to drop that gun… you could have ended all of this earlier, you know?"

With Dean frozen in place and glaring daggers at Jack, the hunter moved closer, feeling confident now that he had a loaded gun aimed at the teen's head, ready to pull the trigger if that's what was needed.

Dean's nostrils were flaring with barely repressed anger as he tried to keep his emotions in check.

"I knew you were bluffing…" the teen pressed out from behind clenched teeth, whole body coiled tight with hatred.

Jack only chuckled in response. "Well good on you Dean. Even more of a fuck-up then, if you ask me."

"Yeah but you know what?" Dean snidely shot back. "His gun wasn't the only thing I found back there, you _sick son of a bitch_—"

Dean was moving too fast for Jack to react.

His eyes widened drastically when he saw the glinting knife in Dean's hand but by then it was already too late. The sharp steel blade cut into his flesh like a knife cutting butter, burying itself in Jack's side with a sickening sound.

Jack screamed and staggered backwards when a blinding white agony blossomed before his eyes. He squeezed his eyes shut against the onslaught of pain, blindly grasping for the knife protruding from the side of his stomach, but Dean didn't give him any time to recover.

Pouncing on him, the teen knocked Jack to the ground and landed a solid punch to his chin.

Jack tried to retaliate, lashing out at the teen but Dean caught his arm and twisted it brutally in his grasp, forcing him to let go of the gun in his hands.

"You little fucker—" Jack growled viciously, trying to reclaim his hold on the weapon, but Dean kicked him in the stomach, rendering him immobilized and gasping for breath.

"What is it, Jack? Can't catch your breath?" Dean sneered into his face, leaning in close enough for Jack to see the fury in his intense gaze. "Well ain't that a bitch…"

Another kick to the kidneys had Jack groaning in pain and trying to curl up to protect his side. "Y-you won't kill me… n-not while your brother's watchin'…"

Dean huffed out a humorless chuckle at that.

"You mean my baby brother, Sam, whose arm you dislocated? The kid you very nearly _choked to death_ not even 15 minutes ago, _that's_ who you're talking about?!"

Dean's fist slammed his head backwards against the cemented floor of the basement, sending stars dancing through his vision. The teenager grabbed him by the lapels of his shirt and pulled him up close enough before slamming him back down to the ground and rattling his whole body to the core.

"You're right… Sammy wouldn't want me to kill you," Dean hissed into the hunter's ear. "He's the kind of pure soul that would forgive you- no matter what you did to him—hell the kid would probably find reasons to justify your actions if it would spare your pathetic excuse of a life. _Me_ on the other hand—" Dean's whole face changed into a mask of rage before landing a final blow to knock Jack out.

"I'm not that forgiving..."

**TBC...**

* * *

_Sorry for the long wait, guys, I've been in Berlin on a business trip and got held up with work. Feeling kind of frustrated and down lately... which naturally results in a_ _bad case of writer's block. To be honest I am not sure this chapter turned out alright... hope it didn't dissappoint. Everybody who's following me, probably already knows my stories get more brutal when my frustration level rises :P But oh well... maybe it's just my twisted mind coming up with new ways to torture our favorite boys. I am planning to add 1-2 more chapters to complete this WIP... John will make an appearance as well. And he's not the forgiving type either ;) Just saying._  
_Please tell me what you thought :D Reviews are very much appreciated!_


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